DK173955B1 - Liquid herbicide concentrate and its use in a method for controlling undesirable vegetation - Google Patents
Liquid herbicide concentrate and its use in a method for controlling undesirable vegetation Download PDFInfo
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- DK173955B1 DK173955B1 DK198605048A DK504886A DK173955B1 DK 173955 B1 DK173955 B1 DK 173955B1 DK 198605048 A DK198605048 A DK 198605048A DK 504886 A DK504886 A DK 504886A DK 173955 B1 DK173955 B1 DK 173955B1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
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Abstract
Description
DK 173955 B1DK 173955 B1
Den foreliggende opfindelse angår hidtil ukendte flydende, herbicide koncentrater, der kan fortyndes med vand eller vandholdig væske før anvendelse på marken. Den fytoaktive forbindelse i koncentratet ifølge opfindelsen indeholder gruppen O 0 -c-ch2-n-ch2-pc (I).The present invention relates to novel liquid herbicidal concentrates which can be diluted with water or aqueous liquid prior to use in the field. The phytoactive compound in the concentrate of the invention contains the group O -c-ch2-n-ch2-pc (I).
5 Opfindelsen angår endvidere en fremgangsmåde til bekæmpelse af uønsket vegetation under anvendelse af koncentratet ifølge opfindelsen.The invention further relates to a method for controlling undesirable vegetation using the concentrate of the invention.
De fytoaktive forbindelser indeholdende den ovenfor som formel I angivne gruppe betegnes heri som N-phosphonomethyl-N-carboxy-methylforbindelser eller "PMCM"-forbindelser. Disse forbindel-10 ser og gruppen med formlen I vil blive yderligere defineret og illustreret i det følgende. Af nemheds hensyn vil de fytoaktive forbindelser indeholdende gruppen med formlen I i det følgende blive betegnet som PMCM-forbindelser.The phytoactive compounds containing the group listed above as Formula I are referred to herein as N-phosphonomethyl-N-carboxy-methyl compounds or "PMCM" compounds. These compounds and the group of formula I will be further defined and illustrated below. For convenience, the phytoactive compounds containing the group of formula I will hereinafter be referred to as PMCM compounds.
Der kendes et stort antal fytoaktive PMCM-forbindelser inden 15 for området. Udtrykket "fytoaktiv", som det anvendes til beskrivelse af denne opfindelse, betyder effektiv som en plante-vækstregulator, som et herbicid, som et afløvningsmiddel eller lignende. Illustrative sådanne PMCM-forbindelser og deres anvendelse er beskrevet i US-patentskrifterne nr. 31455.675, 3.799.758, 20 3.556.762, 4.405.531, 3.868.407, 4.140.513, 4.315.765, 4.481.026 og 4.397.676 samt international ansøgning WO 84/03607.A large number of phytoactive PMCM compounds are known in the art. The term "phytoactive" as used in the description of this invention means effective as a plant growth regulator, as a herbicide, as a detergent or the like. Illustrative of such PMCM compounds and their use are disclosed in U.S. Patents Nos. 31455,675, 3,799,758, 20 3,556,762, 4,405,531, 3,868,407, 4,140,513, 4,315,765, 4,481,026 and 4,397,676. as well as international application WO 84/03607.
De fleste af disse patentskrifter omfatter også beskrivelser af fremgangsmåder, der anvendes til fremstilling af sadanne forbindelser. De følgende patentskrifter giver yderligere 2 DK 173955 B1 beskrivelser af fremgangsmåder: US-patentskrifteme nr. 3.288.846,4.507.250,4.147.719 og 4.487.724.Most of these patents also include descriptions of methods used to prepare such compounds. The following patents further disclose methods of U.S. Patent Nos. 3,288,846,4,507,250,4,147,719 and 4,487,724.
Visse PMCM-forbindelser, salte af N-phosphomethylglycin, har vist sig at være særligt effektive som post-emergens-herbicider.Certain PMCM compounds, salts of N-phosphomethylglycine, have been found to be particularly effective as post-emergence herbicides.
5 Sådanne salte af N-phosphomethylglycin, der er særligt effektive som herbicide midler, omfatter trimethylsulfoniumsaltene af N-phosphonomethylglycin som beskrevet i US-patentskrift nr. 4.315.765, de blandede alkylsulfoniumsalte af N-phosphonomethylglycin som beskrevet i US-patentskrift nr. 4.437.874 10 og trialkylsaltene af N-phosphonomethylglycin, der er beskrevet i US-patentskrifterne nr. 4.384.880 og 4.345.765.Such salts of N-phosphomethylglycine which are particularly effective as herbicidal agents include the trimethylsulfonium salts of N-phosphonomethylglycine as described in U.S. Patent No. 4,315,765, the mixed alkylsulphonium salts of N-phosphonomethylglycine as described in U.S. Patent No. 4,437 .874 and the trialkyl salts of N-phosphonomethylglycine disclosed in U.S. Pat. Nos. 4,384,880 and 4,345,765.
Normalt formuleres herbicide midler som puddere, granulære midler, flydende emulsioner eller flydende koncentrater. Saltene af N-phosphonomethylglycin, der anvendes som de aktive bestand-15 dele i herbicider, formuleres fortrinsvis som flydende koncentrater, fordi de faktisk er vandopløselige og hygroskopiske, hvilket gør det vanskeligt at krystallisere dem og isolere dem fra vandopløsninger. Et godt flydende koncentrat udviser god forligelighed for de forskellige bestanddele, god varmestabili-20 tet og god stabilitet ved langtids-lagring samt blandbarhed af den aktive bestanddel med det flydende opløsningsmiddel. Desuden skal det have minimal irritation af øjet og lave inhalerings-irritationsniveauer. Ikke alle flydende koncentrater, der indeholder saltene af N-phosphonomethylglycin som aktiv 25 bestanddel, har disse egenskaber.Usually herbicidal agents are formulated as powders, granular agents, liquid emulsions or liquid concentrates. The salts of N-phosphonomethylglycine used as the active ingredients in herbicides are preferably formulated as liquid concentrates because they are actually water-soluble and hygroscopic, making it difficult to crystallize them and isolate them from water solutions. A good liquid concentrate exhibits good compatibility for the various components, good heat stability and good long-term storage stability, and miscibility of the active ingredient with the liquid solvent. In addition, it should have minimal eye irritation and low inhalation irritation levels. Not all liquid concentrates containing the salts of N-phosphonomethylglycine as active ingredient have these properties.
Den nærmestliggende kendte teknik anses for at være beskrevet i ovennævnte US-patentskrift nr. 4.315.765 samt i US-patentskrift nr. 3.799.758.The prior art is considered to be described in the above-mentioned U.S. Patent No. 4,315,765 and in U.S. Patent No. 3,799,758.
3 DK 173955 B1 I US-patentskrift nr. 4.315.765 beskrives forskellige trialkylsulfoniumsalte afN-phospho-nomethylglycin. Endvidere beskrives et antal formuleringstyper, herunder puddere, opløs* ninger, emulgerbare koncentrater og befugtelige pulvere. En liste med forskellige ikke-ioniske overfladeaktive midler er angivet, men der findes ingen henvisning til alkylpoly-5 glycosider som en løsning på problemet med opnåelse af fortyndingsklare herbicide koncentrater.US Patent No. 4,315,765 discloses various trialkylsulfonium salts of N-phosphonomethylglycine. Also described are a number of formulation types, including powders, solutions, emulsifiable concentrates and wettable powders. A list of various nonionic surfactants is provided, but there is no reference to alkyl polyglycosides as a solution to the problem of obtaining dilute clear herbicidal concentrates.
I US-patentskrift nr. 3.799.758 angives, at der eksisterer et antal forskellige formuleringer med glyphosat. En liste over mulige overfladeaktive midler opregnes i dette patentskrift.U.S. Patent No. 3,799,758 states that a number of different glyphosate formulations exist. A list of possible surfactants is listed in this patent.
Der findes imidlertid ingen anvisning, som vil gøre det muligt for gennemsnitsfagmanden 10 at udvælge et alkylpolyglycosid som løsning på problemet med at tilvejebringe et fortyndingsklart, herbicidt koncentrat.However, there is no indication that would allow the skilled artisan 10 to select an alkyl polyglycoside as a solution to the problem of providing a dilute clear herbicide concentrate.
Formålet: med denne opfindelse er derfor at tilvejebringe et fy toaktivt middel i form af et flydende koncentrat, hvor der som aktiv bestanddel anvendes en PMCM-forbindelse, fortrinsvis 15 et landbrugsmæssigt acceptabelt salt af N-phosphonomethylglycin, og et ikke-ionisk, overfladeaktivt middel.The object: therefore, of this invention is to provide a phytoactive agent in the form of a liquid concentrate, using as an active ingredient a PMCM compound, preferably an agriculturally acceptable salt of N-phosphonomethylglycine, and a nonionic surfactant. .
Den foreliggende opfindelse angår en flydende, fytoaktiv formulering, der som aktiv bestanddel indeholder en N—phosphonomethyl— N-carboxymethylforbindelse opløst eller dispergeret i et egnet 20 medium, og et flydende, ikke-ionisk, overfladeaktivt middel. Formuleringen kan fortyndes med vand eller en vandholdig væske før anvendelse på marken.The present invention relates to a liquid, phytoactive formulation containing as active ingredient an N-phosphonomethyl-N-carboxymethyl compound dissolved or dispersed in a suitable medium, and a liquid, nonionic surfactant. The formulation can be diluted with water or an aqueous liquid before use in the field.
Formuleringen ifølge denne opfindelse har den fordel, at den kan indeholde en stor mængde aktiv bestanddel, er termisk sta- 4 DK 173955 B1 bil over et bredt temperaturinterval, er forligelig med og for-tyndbar i både hårdt og blødt vand og også er forligelig og fortyndbar med en nitrogenholdig kunstgødningsopløsning samt irriterer øjnene minimalt. Formuleringen ifølge denne opfindel-5 se er også stabil ved ældning over måneders lagring over et bredt temperaturinterval. Desuden hidrører de ikke-ioniske, overfladeaktive midler fra naturligt forekommende produkter og nedbrydes let af mikroorganismer.The formulation of this invention has the advantage that it can contain a large amount of active ingredient, is thermally stable over a wide temperature range, is compatible with and dilutable in both hard and soft water, and is also compatible. diluted with a nitrogenous fertilizer solution as well as minimally irritating the eyes. The formulation of this invention is also stable in aging over months of storage over a wide range of temperatures. In addition, the nonionic surfactants are derived from naturally occurring products and are readily degraded by microorganisms.
Opfindelsen angår derfor et hidtil ukendt herbicidt koncentrat, der kan fortyndes med vand 10 eller vandholdig væske før anvendelse på marken, hvilket koncentrat er ejendommeligt ved, at det omfatter: (a) en herbicidt effektiv N-phosphonomethyl-N-carboxymethylforbindelse, (b) et eller flere flydende, ikke-ioniske, overfladeaktive midler, som er valgt blandt alkyl-polyglycosider, 15 (c) et opløsningsmiddel for N-phosphonomethyl-N-carboxymethylforbindelsen, og (d) et eller flere inerte hjælpestoffer.The invention therefore relates to a novel herbicidal concentrate which can be diluted with water 10 or aqueous liquid prior to use in the field, which concentrate is characterized in that it comprises: (a) a herbicidally effective N-phosphonomethyl-N-carboxymethyl compound, (b) one or more liquid, nonionic surfactants selected from alkyl polyglycosides, (c) a solvent for the N-phosphonomethyl-N-carboxymethyl compound, and (d) one or more inert auxiliaries.
Fremgangsmåden ifølge opfindelsen omfatter, at man anvender en herbicidt effektiv mængde af det ovenfor beskrevne koncentrat på det sted, hvor bekæmpelse ønskes. Normalt ville dette være på bladene af det skadelige ukrudt, der skal udryddes.The method of the invention comprises using a herbicidally effective amount of the concentrate described above at the site where control is desired. Usually this would be on the leaves of the harmful weed to be eradicated.
20 Enhver væskedispergerbar, fytoaktiv PMCM-forbindelse kan anvendes i midlerne og fremgangsmåden ifølge opfindelsen. Udtrykket "væskedispergerbar" anvendes i bred forstand til at omfatte for- 5 ! DK 173955 B1 bindeiser, som er opløselige i en væske, samt forbindelser, som blot er dispergerbare. I foretrukne udførelsesformer er PMCM-forbindelsen væskeopløselig. I den mest foretrukne udførelsesform er den vandopløselig.Any liquid dispersible, phytoactive PMCM compound can be used in the agents and methods of the invention. The term "liquid dispersible" is used in a broad sense to include precursors. B1 binders which are soluble in a liquid, as well as compounds which are merely dispersible. In preferred embodiments, the PMCM compound is liquid soluble. In the most preferred embodiment, it is water soluble.
5 PMCM-forblndelserne kan repræsenteres ved formlen 0 Z 0 r-c-ch2n-ch2p- (R) 2 hvori R er valgt blandt halogen, -NHOH, -N(R^") ~f -OR2, -SR2 og 1 * -OM., hvor R uafhængigt er valgt blandt hydrogen, alkyl eller hydroxy- alkyl, fortrinsvis indeholdende færre end ca. 5 carbonatomer, alkenyl, fortrinsvis indeholdende færre end ca. 5 carbonatomer , 10 eller phenyl, R uafhængigt er valgt blandt hydrogen, alkyl, hydroxyalkyl og chloralkyl, fortrinsvis indeholdende færre end ca. 5 carbonatomer, alkoxy, fortrinsvis indeholdende færre end ca. 5 carbonatomer, alkylenamin, fortrinsvis indeholdende færre end ca. 12 carbonatomer, phenyl eller benzyl, og M er valgt blandt hydrogen 15 og landbrugsmæssigt acceptable, saltdannende grupper, såsom alkalimetal-, jordalkalimetal-, stanni-, ammonium-, organiske ammonium-, alkylsulfonium-, alkylsulfoxonium-, alkylphosphonlum-grupper eller kombinationer deraf, og Z er hydrogen, en organisk gruppe eller en uorganisk gruppe.The PMCM bleaches may be represented by the formula 0 Z 0 rc-ch 2 n-ch 2 p - (R) 2 wherein R is selected from halogen, -NHOH, -N (R 2 ") ~ f -OR 2, -SR 2 and 1 * -OM wherein R is independently selected from hydrogen, alkyl or hydroxyalkyl, preferably containing less than about 5 carbon atoms, alkenyl, preferably containing less than about 5 carbon atoms, or phenyl, R is independently selected from hydrogen, alkyl, hydroxyalkyl and chloroalkyl, preferably containing less than about 5 carbon atoms, alkoxy, preferably containing less than about 5 carbon atoms, alkyleneamine, preferably containing less than about 12 carbon atoms, phenyl or benzyl, and M is selected from hydrogen and agriculturally acceptable salt forming groups such as alkali metal, alkaline earth metal, stannic, ammonium, organic ammonium, alkylsulfonium, alkylsulfoxonium, alkylphosphonium groups or combinations thereof, and Z is hydrogen, an organic group or an inorganic group.
20 Repræsentative patentskrifter, hvori i det mindste nogle af sådanne forbindelser er beskrevet, omfatter US-patentskrifterne nr. 3.799.758, 4.397.676, 4.140.513, 4.315.765, 3.868.407, .Representative patents describing at least some of such compounds include U.S. Patent Nos. 3,799,758, 4,397,676, 4,140,513, 4,315,765, 3,868,407,
4.405.531, 4.481.026, 4.414.158, 4.120.689, 4.472.189, 4.341.549 og 3.948.975.4,405,531, 4,481,026, 4,414,158, 4,120,689, 4,472,189, 4,341,549 and 3,948,975.
25 Repræsentative patentskrifter, hvori beskrives PMCM-forbindelser, hvor Z er forskellig fra hydrogen, omfatter US-patentskrifter-ne nr. 3.888.915, 3.933.946, 4.062.699, 4.119.430, 4.322.239 og 4.084.954.Representative patents describing PMCM compounds wherein Z is different from hydrogen include U.S. Patent Nos. 3,888,915, 3,933,946, 4,062,699, 4,119,430, 4,322,239 and 4,084,954.
6 DK 173955 B1 I foretrukne PMCM-forbindelser er Z hydrogen eller en organisk substituent. Repræsentative organiske substituenter omfatter methylencarboxyl-, methylenphosphon-, methylencyano-, carbonyl- ,1 såsom formyl-, acetyl-, benzoyl-, perfluoracyl— og· thiocarbonyl-, ethylen- såsom cyano-, carbamoyl- eller carboxysubstitueret 5 ethyl- og benzensulfonylsubstituenter. Repræsentative patentskrifter, hvori beskrives forbindelser, hvor nitrogenatomet indeholder tre organiske substituenter, omfatter US-patent-skrifterne nr. 3.455.675, 3.556.762, 3.853.530, 3.970.695, 3.988.142, -3.991.095, 3.996.040, 4.047.927, 4.180.394, 4.203.756, 10 4.261.727 og 4.312.662. En foretrukket tertiær, nitrogen substitueret PMCM-forbindelse er N,N-bis(phosphonomethyl)glycin.In preferred PMCM compounds, Z is hydrogen or an organic substituent. Representative organic substituents include methylene carboxyl, methylene phosphone, methylene cyano, carbonyl, such as formyl, acetyl, benzoyl, perfluoroacyl and thiocarbonyl, ethylene such as cyano, carbamoyl or carboxy substituted ethyl and benzenesulfonylsubstituted. Representative patents describing compounds wherein the nitrogen atom contains three organic substituents include U.S. Patent Nos. 3,455,675, 3,556,762, 3,853,530, 3,970,695, 3,988,142, -3,991,095, 3,996,040. , 4,047,927, 4,180,394, 4,203,756, 4,216,727 and 4,312,662. A preferred tertiary, nitrogen-substituted PMCM compound is N, N-bis (phosphonomethyl) glycine.
De PMCM-forbindelser, hvori Z er hydrogen, er mest foretrukket, når den ønskede fytoaktivitet er herbicid aktivitet.The PMCM compounds wherein Z is hydrogen are most preferred when the desired phytoactivity is herbicidal activity.
1515
Illustrative, landbrugsmæssigt acceptable saltdannende grupper, der repræsenteres ved M, såsom i OM, er alkalimetallerne med atomvægte fra 22 til 133 inklusive, såsom natrium, kalium eller rubidium, jordalkalimetallerne med atomvægte fra 24 til 88 in-20 klusive, såsom magnesium eller calcium, ammonium og alifatisk ammonium, hvor den alifatiske ammonium er primær, sekundær, tertiær eller kvaternær, og fortrinsvis hvori det totale antal carbonatomer ikke overskrider mere end ca. 12, phenylammonium, trialkylsulfonium, fortrinsvis hvori det totale antal carbon-25 atomer i de tre alkylsubstituenter ikke overskrider mere end ca. 6, såsom trimethylsulfonium, ethyldimethylsulfonium, propyl-dimethylsulfonium og lignende, trialkylsulfoxonium, fortrinsvis hvori det totale antal carbonatomer i de tre alkylsubstituenter ikke overskrider mere end ca. 6, såsom trimethylsulfoxonium, 30 ethyldimethylsulfoxonium, propyldimethylsulfoxonium og lignende, 7 DK 173955 B1 tetraalkylphosphonium, såsom tetramethylphosphonium, ethyl-trimethylphosphonium, propyltrimethylphosphonium og lignende.Illustrative, agriculturally acceptable salt-forming groups represented by M, such as in OM, are the alkali metals with atomic weights from 22 to 133 inclusive, such as sodium, potassium or rubidium, the alkaline earth metals with atomic weights from 24 to 88 inclusive, such as magnesium or calcium, ammonium and aliphatic ammonium, wherein the aliphatic ammonium is primary, secondary, tertiary or quaternary, and preferably wherein the total number of carbon atoms does not exceed more than ca. 12, phenylammonium, trialkylsulfonium, preferably wherein the total number of carbon atoms in the three alkyl substituents does not exceed more than ca. 6, such as trimethylsulfonium, ethyldimethylsulfonium, propyl-dimethylsulfonium and the like, trialkylsulfoxonium, preferably wherein the total number of carbon atoms in the three alkyl substituents does not exceed about 6 such as trimethylsulfoxonium, ethyldimethylsulfoxonium, propyldimethylsulfoxonium and the like, tetraalkylphosphonium such as tetramethylphosphonium, ethyl trimethylphosphonium, propyltrimethylphosphonium and the like.
Det skal bemærkes, at jordalkalimetalsaltene kun giver underordnet herbicid aktivitet, selv om de er landbrugsmæssigt accep-5 table.It should be noted that the alkaline earth metal salts only provide inferior herbicidal activity, although they are agriculturally acceptable.
I foretrukne midler ifølge denne opfindelse er M uafhængigt valgt blandt de ovenfor beskrevne landbrugsmæssigt acceptable, saltdannende grupper og hydrogen. I mere foretrukne midler er M et alkalimetal, ammonium, monoalkylammonium eller trialkylsulfonium.In preferred agents of this invention, M is independently selected from the agricultural described salt-forming groups and hydrogen described above. In more preferred agents, M is an alkali metal, ammonium, monoalkylammonium or trialkylsulfonium.
10 I de mest foretrukne midler er kun ét M et alkalimetal, ammonium, monoalkylammonium eller trialkylsulfonium, mens de to andre M'er er hydrogen. Repræsentative, mest foretrukne midler omfatter isopropylamin-N-phosphonomethylglycin, trimethylsulfonium-N-phos-phonomethylglycin og natriumsesqui-N-phosphonomethylglycin. Kom-15 binationer af to eller flere PMCM-forbindelser kan anvendes i midlerne og fremgangsmåderne ifølge opfindelsen.In the most preferred agents, only one M is an alkali metal, ammonium, monoalkylammonium or trialkylsulfonium, while the other two M's are hydrogen. Representative, most preferred agents include isopropylamine-N-phosphonomethylglycine, trimethylsulfonium-N-phosphonomethylglycine, and sodium sesqui-N-phosphonomethylglycine. Combinations of two or more PMCM compounds can be used in the agents and methods of the invention.
De flydende, ikke-ioniske, overfladeaktive midler, der anvendes som en af de essentielle komponenter af de herbicide midler ifølge opfindelsen, kan f.eks. være en hvilken som helst af de 20 følgende specifikke forbindelsers AL-1685 og AL-2042, der sælges af ICI, Emcol D-7533 og Witcamide 272 (et modificeret alkanol-amid), der sælges af Witco Chemical Company, Staley APG 91-3,The liquid, nonionic surfactants used as one of the essential components of the herbicidal compositions of the invention can be e.g. be any of the following 20 specific compounds AL-1685 and AL-2042 sold by ICI, Emcol D-7533 and Witcamide 272 (a modified alkanol amide) sold by Witco Chemical Company, Staley APG 91- 3
Staley APG 91-1, Staley APG 23-1 og Staley APG 23-3, alle alkyl-polyglycosider, der sælges af Staley Corporation, og Crodesta 25 SL-40, et monococoat, der sælges af Croda Inc. Et typisk over fladeaktivt APG-middel har den gentagne strukturelle formelStaley APG 91-1, Staley APG 23-1 and Staley APG 23-3, all alkyl polyglycosides sold by Staley Corporation, and Crodesta 25 SL-40, a monococoat sold by Croda Inc. A typical surfactant APG agent has the repetitive structural formula
CH2OH CHjOBCH 2 OH CH 2 OB
Q_. OQ_. ISLAND
db T—^—a-1 T-yjjcBjjrfHa 8 DK 173955 B1db T - ^ - a-1 T-yjjcBjjrfHa 8 DK 173955 B1
Hvilke som helst af to (eller flere) af de ovennævnte ikke-ioniske, overfladeaktive midler kan blandes i forskellige forhold og anvendes i det herbicide middel til opnåelse af bedre fysisk overfladeaktive egenskaber, end når de hver anvendes 5 alene. Et eksempel er kombinationen af AL-1685 og APG 91-3 i et forhold på 60:40 eller 70:30.Any of two (or more) of the aforementioned nonionic surfactants can be mixed in different ratios and used in the herbicidal agent to achieve better physical surfactant properties than when each is used alone. An example is the combination of AL-1685 and APG 91-3 at a ratio of 60:40 or 70:30.
Ud over de foregående kan der også inkorporeres inerte hjælpestoffer i midlerne ifølge denne opfindelse for at tilvejebringe en mere tilfredsstillende formulering. Sådanne inerte hjælpe-10 stoffer omfatter antiskummidler, fortrinsvis dimethylpolysil-oxan, pyrogene silica som et fortykkelsesmiddel og eventuelt vand.In addition to the foregoing, inert auxiliaries may also be incorporated into the agents of this invention to provide a more satisfactory formulation. Such inert auxiliaries include antifoam agents, preferably dimethylpolysiloxane, pyrogenic silica as a thickening agent and optionally water.
Vægtprocenten af den aktive PMCM-forbindelse i de flydende koncentrater ifølge denne opfindelse kan variere fra ca. 10 til ca. 15 70 vægt%, fortrinsvis fra ca. 30 til ca. 40 vægt% og mest fore trukket fra ca. 38 til ca. 42 vægt%.The weight percent of the active PMCM compound in the liquid concentrates of this invention can range from about 10 to approx. About 70% by weight, preferably from ca. 30 to approx. 40% by weight and most preferred from approx. 38 to approx. 42% by weight.
De ikke-ioniske, overfladeaktive midler, der anvendes i midlerne ifølge denne opfindelse, kan variere fra ca. 5 til ca. 40 vægt%, fortrinsvis fra ca. 15 til ca. 30 vægt% og mest foretrukket fra 20 ca. 15 til ca. 25 vægt%.The nonionic surfactants used in the compositions of this invention can range from approx. 5 to approx. 40% by weight, preferably from approx. 15 to approx. 30% by weight and most preferably from about 20%. 15 to approx. 25% by weight.
Den mængde inert hjælpestof, der anvendes i midlerne ifølge denne opfindelse, kan variere fra ca. 0,5 til ca. 10 vægt%, fortrinsvis fra ca. 1 til ca. 5 vægt% og mest foretrukket fra ca.The amount of inert auxiliary used in the agents of this invention may vary from ca. 0.5 to approx. 10% by weight, preferably from approx. 1 to approx. 5% by weight and most preferably from approx.
1 til ca. 3 vægt%.1 to approx. 3% by weight.
25 Vand eller andet væskemedium udgør resten af det flydende koncentrat. Den kan variere fra ca. 10 til ca. 70 vægt%, fortrinsvis fra ca. 20 til ca. 50 vægt%.25 Water or other liquid medium constitutes the remainder of the liquid concentrate. It can vary from approx. 10 to approx. 70% by weight, preferably from ca. 20 to approx. 50% by weight.
9 DK 173955 B19 DK 173955 B1
De fytoaktive midler ifølge opfindelsen kan fremstilles ved at fremstille en opløsning af den aktive PMCM-forbindelse og dertil sætte det ikke-ioniske, overfladeaktive middel, de eventuelle tilsætningsstoffer og så meget yderligere dispergeringsmid-5 del, som der kræves. Det foretrukne dispergeringsmiddel er vand.The phytoactive agents of the invention can be prepared by preparing a solution of the active PMCM compound and adding thereto the nonionic surfactant, any additives, and as much additional dispersant as required. The preferred dispersant is water.
Fordelene ved anvendelsen af ikke-ionisk, overfladeaktivt middel i fremgangsmåden og midlerne ifølge denne opfindelse er, at de generelt er billige, nemt tilgængelige, ringe eller ikke-irriterende, ofte med lav toksicitet over for pattedyr og generelt er 10 ringe eller ikke-skummende, og eftersom de hidrører fra naturligt frembragte produkter, nedbrydes de nemt af mikroorganismer.The advantages of using nonionic surfactant in the process and agents of this invention are that they are generally inexpensive, readily available, poor or non-irritating, often with low toxicity to mammals, and are generally low or non-foaming. , and because they are derived from naturally produced products, they are easily degraded by microorganisms.
Som tidligere angivet, kan der om ønsket også anvendes blandinger af forskellige ikke-ioniske, overfladeaktive midler.As previously indicated, mixtures of various nonionic surfactants may also be used if desired.
De foretrukne fytoaktive midler ifølge denne opfindelse har en 15 herbicidt aktiv bestanddel.The preferred phytoactive agents of this invention have a herbicidal active ingredient.
Herefter følger eksempler på forskellige formuleringer af de herbicide midler ifølge denne opfindelse.Following are examples of various formulations of the herbicidal agents of this invention.
Bestanddel Vægt% (a.b.**) 1. X-100* (72%) 57,2 (41,2) 20 AL-2042 (100%) 10,3 (10,3)Component Weight% (a.b. **) 1. X-100 * (72%) 57.2 (41.2) 20 AL-2042 (100%) 10.3 (10.3)
Staley APG 91-3 (57%) 18,1 (10,3)Staley APG 91-3 (57%) 18.1 (10.3)
Vand 14,4 100,0%Water 14.4 100.0%
SS'jSSSSSSSS'jSSSSSS
DK 173955 B1DK 173955 B1
Bestanddel Vægt% 10.Ingredient Weight% 10.
, -i- XX, (a.b. ) 2. X-100 (56%) 73,3 (41,2) AL-2042 (100%) 20,6x-100 (56%) 73.3 (41.2) AL-2042 (100%) 20.6
Vand 6,1 100,0% 5 3. X-100 (72%) 57,2 (41,2)Water 6.1 100.0% 5 3. X-100 (72%) 57.2 (41.2)
Staley APG 91-3 (57%) 36,1 (20,6)Staley APG 91-3 (57%) 36.1 (20.6)
Vand 6,7 100,0% 4. X-100 (72%) 57,2 (41,2) AL-1685 (100%) 10,3 (10,3) 10 Staley APG 91-3 (57%) 18,1 (10,3)Water 6.7 100.0% 4. X-100 (72%) 57.2 (41.2) AL-1685 (100%) 10.3 (10.3) Staley APG 91-3 (57%) 18.1 (10.3)
Vand 14,4 100,0%Water 14.4 100.0%
BBBSBSBBBSBS
5. X-100 (57%) 51,8 (29,5)5. X-100 (57%) 51.8 (29.5)
Staley APG 91-3 (70%) 48,2 (33,9) 100,0% 6. X-100 (57%) 53,0 (30,2) 15 Staley APG 91-3 (57%) 47,0 (26,8) 100,0% 7. X-100 (57,3%) 71,9 (41,2)Staley APG 91-3 (70%) 48.2 (33.9) 100.0% 6. X-100 (57%) 53.0 (30.2) Staley APG 91-3 (57%) 47, 0 (26.8) 100.0% 7. X-100 (57.3%) 71.9 (41.2)
Spraytørret Staley 23-3 (100%) 20,6Spray-dried Staley 23-3 (100%) 20.6
Vand ' 7,5 100,0% sssrssWater '7.5 100.0% sssrss
Bestanddel Vægt% 11 DK 173955 B1 (a.b.XX) 8. X-100 (72%) 57,2 (41r2)Component Weight% 11 DK 173955 B1 (a.b.XX) 8. X-100 (72%) 57.2 (41r2)
Staley APG 23-1 (53%) 38,9 (20,6)Staley APG 23-1 (53%) 38.9 (20.6)
Vand 3,9 100,0% 5 9. X-100 (72%) 57,2 (41,2)Water 3.9 100.0% 5 9. X-100 (72%) 57.2 (41.2)
Staley APG 23-3 (46%) 42,8 (19,7) 100,0% 10. X-100 (72%) 57,2 (41,2)Staley APG 23-3 (46%) 42.8 (19.7) 100.0% 10. X-100 (72%) 57.2 (41.2)
Staley APG 91-1 (51%) 40,4 (20,6)Staley APG 91-1 (51%) 40.4 (20.6)
Vand 2,4 100,0% 10 11. X-100 (72%) 57,2 (41,2)Water 2.4 100.0% 10 11. X-100 (72%) 57.2 (41.2)
Staley APG 91-3 (57%) 36,1 (20,6)Staley APG 91-3 (57%) 36.1 (20.6)
Vand 6,7 100,0%Water 6.7 100.0%
B33C5BB33C5B
12. X-100 (57%) 71,9 (41,2) AL-2042 (100%) 20,6 15 Vand 7,5 100,0% 13. X-100 (57%) 54,3 (31,2) AL-2042 (100%) 31,212. X-100 (57%) 71.9 (41.2) AL-2042 (100%) 20.6 15 Water 7.5 100.0% 13. X-100 (57%) 54.3 (31 , 2) AL-2042 (100%) 31.2
Vand 14,5 '100,0% ssssss DK 173955 B1 12Water 14.5 '100.0% ssssss DK 173955 B1 12
Bestanddel Vægt% / U. XX\ (a.b. ) 14. X-100 (57%) 66,4 (38,2)Ingredient Weight% / U XX \ (a.b.) 14. X-100 (57%) 66.4 (38.2)
Emcol D-7533 (Witco) 19/1Emcol D-7533 (Witco) 19/1
Vand 14,5 100,0% 5 15..X-100 (57%) 54,3 (31,2)Water 14.5 100.0% 5 15.X-100 (57%) 54.3 (31.2)
Emcol D-7533.(Witco) 31,2Emcol D-7533 (Witco) 31.2
Valid 14,5 100,0% 16. X-100 (57%) 54,3 (31,2) AL-2041 31,2 10 Vand 14,5 100,0% 17. X-100 (57%) 63,2 (36,3) AL—2042 27,3Valid 14.5 100.0% 16. X-100 (57%) 54.3 (31.2) AL-2041 31.2 10 Water 14.5 100.0% 17. X-100 (57%) 63 , 2 (36.3) AL-2042 27.3
Vand 9,5 100,0% ssssess 18. X-100 (57%) 71,9 (41,2) 15 AL-1685 20,6Water 9.5 100.0% ssssess 18. X-100 (57%) 71.9 (41.2) AL-1685 20.6
Vand 7,5 100,0% 19. X-100 (57%) 71,9 (41,2)Water 7.5 100.0% 19. X-100 (57%) 71.9 (41.2)
Staley APG 91-3 20,6Staley APG 91-3 20.6
Vand - 7,5 .100,0% DK 173955 B1 13Water - 7.5 .100.0% DK 173955 B1 13
Bestanddel Vægt% (a.b.xx) 20. X-100 (57%) 71,9 (41,2) AL-2041 20,6Component Weight% (a.xx.) 20. X-100 (57%) 71.9 (41.2) AL-2041 20.6
Vand 7,5 100,0%Water 7.5 100.0%
SSSSSBSSSSSB
5 21. X-100 (57%) 71,9 (41,2)21. X-100 (57%) 71.9 (41.2)
Emcol D-7533 20,6Emcol D-7533 20.6
Vand 7,5 100,0% 22. X-100 (57%) 71,9 (41,2)Water 7.5 100.0% 22. X-100 (57%) 71.9 (41.2)
Emcol D-7533 20,6 10 Vand 7,5 100,0% 23. X-100 (57,5%) 71,7 (41,2)Emcol D-7533 20.6 10 Water 7.5 100.0% 23. X-100 (57.5%) 71.7 (41.2)
Staley APG 23-3 20,6Staley APG 23-3 20.6
Vand 7,7 100,0% ssacsa 24. X-100 (57%) 71,9 15 AL-1685 (ICI) 20,6Water 7.7 100.0% ssacsa 24. X-100 (57%) 71.9 AL-1685 (ICI) 20.6
Vand 7,5 100,0% 25. X-100 (57,5%) 71,7 (41,2)Water 7.5 100.0% 25. X-100 (57.5%) 71.7 (41.2)
Staley APG 91-1 20,6Staley APG 91-1 20.6
Vand 7,7 100,0%Water 7.7 100.0%
Bestanddel Vægt% DK 173955 B1 14 (a.b.**) 26. X-100 (57,5%) 71,7 (41,2)Component Weight% DK 173955 B1 14 (a.b. **) 26. X-100 (57.5%) 71.7 (41.2)
Staley APG 91-3 20,6Staley APG 91-3 20.6
Vand 7,7 100,0% r=====s= 5 27. X-100 (57,5%) 71,7 (41,2)Water 7.7 100.0% r ===== s = 5 27. X-100 (57.5%) 71.7 (41.2)
Staley APG 23-1 20,6Staley APG 23-1 20.6
Vand 7,7 100,0% cesses x X-100 = trimethylsulfoniumsaltet af N-phosphonomethylglycin i vandig opløsning.Water 7.7 100.0% cesses x X-100 = the trimethylsulfonium salt of N-phosphonomethylglycine in aqueous solution.
XXXX
10 a.b. refererer til aktiv bestanddel.10 a.b. refers to active ingredient.
Ud over PMCM-forbindelsen og det overfladeaktive middel kan midlet også omfatte andre konventionelle hjælpestoffer såsom varmestabilisatorer, midler, der absorberer ultraviolet lys, dispergeringsmidler og andre landbrugsmæssigt acceptable mate-15 rialer. Repræsentative varmestabilisatorer omfatter phenylen-diaminer, phenazin og butyleret hydroxytoluen. Repræsentative midler, der absorberer ultraviolet lys, omfatter Tinuvin 770, Ti,nuvin p og dinitroaniliner.In addition to the PMCM compound and the surfactant, the agent may also comprise other conventional adjuvants such as heat stabilizers, ultraviolet light absorbers, dispersants, and other agriculturally acceptable materials. Representative heat stabilizers include phenylene diamines, phenazine and butylated hydroxytoluene. Representative agents that absorb ultraviolet light include Tinuvin 770, Ti, nuvin p and dinitroanilines.
Forholdet mellem PMCM-forbindelse og overfladeaktivt middel kan 20 variere over et bredt interval. Eftersom det er kendt, at valget af et bestemt overfladeaktivt middel kan påvirke fytoaktiviteten af de PMCM-forbindelser, der anvendes i overensstemmelse med denne opfindelse, bør den ønskede aktivitet af det flydende middel tages i betragtning, når der vælges et bestemt overflade-25 aktivt middel. Der kan anvendes så meget overfladeaktivt middel, 15 DK 173955 B1 j som det ønskes, så længe produkterne opløses totalt eller let dispergeres i fortyndlngsmidlet før anvendelse. Af omkostningshensyn bør der anvendes den minimale mængde overfladeaktivt middel, som stadig muliggør, at formålene med opfindelsen kan 5 opnås. Forholdet mellem PMCM-forbindelse og overfladeaktivt middel er på vægtbasis typisk fra ca. 10:1 til ca. 1:10. Det foretrukne forhold er fra ca. 4:1 til ca. 1:2. Det mest foretrukne forhold er fra ca. 2:1 til ca. 1:1.The ratio of PMCM compound to surfactant may vary over a wide range. Since it is known that the choice of a particular surfactant can affect the phytoactivity of the PMCM compounds used in accordance with this invention, the desired activity of the liquid agent should be taken into account when selecting a particular surfactant. agent. As much surfactant can be used as desired, as long as the products dissolve completely or are easily dispersed in the diluent before use. For the sake of cost, the minimum amount of surfactant should still be used which still enables the objects of the invention to be achieved. The ratio of PMCM compound to surfactant is typically on a weight basis ranging from approx. 10: 1 to approx. 1:10. The preferred ratio is from approx. 4: 1 to approx. 1: 2. The most preferred ratio is from approx. 2: 1 to approx. 1: 1.
Midlerne ifølge denne opfindelse kan fremstilles på enhver egnet 10 måde. En foretrukket fremgangsmåde omfatter imidlertid, at man først fremstiller en blanding indeholdende PMCM-forbindelsen og dispergeringsmidlet. I foretrukne udførelsesformer opløses PMCM-forbindelsen i midlet. I andre udførelsesformer dispergeres PMCM-forbindelsen deri.The agents of this invention can be prepared in any suitable manner. However, a preferred method involves first preparing a mixture containing the PMCM compound and the dispersant. In preferred embodiments, the PMCM compound is dissolved in the agent. In other embodiments, the PMCM compound is dispersed therein.
15 I nogle udførelsesformer fremstilles blandingen ved at danne PMCM-forbindelsen in situ. For eksempel omsættes N-phosphono-methylglycin i nogle udførelsesformer med en ønsket base i nærværelse af vand til dannelse af en vandig opløsning indeholdende PMCM-forbindelsen. I foretrukne udførelsesformer kan opløsninger 20 af isopropylamin-N-phosphonomethylglycin fremstilles på denne måde.In some embodiments, the mixture is prepared by forming the PMCM compound in situ. For example, in some embodiments, N-phosphono-methylglycine is reacted with a desired base in the presence of water to form an aqueous solution containing the PMCM compound. In preferred embodiments, solutions 20 of isopropylamine-N-phosphonomethylglycine can be prepared in this way.
Dispergeringsmidlet, der skal anvendes i overensstemmelse med fremgangsmåden ifølge denne opfindelse, må opfylde visse krav.The dispersant to be used in accordance with the method of this invention must meet certain requirements.
Midlet må være i stand til at opløse eller dispergere en ønsket 25 PMCM-forbindelse ved den temperatur, der anvendes til dannelse af den oprindelige blanding, uden negativt at påvirke PMCM-forbindelsens fytoaktivitet. Jo større opløseligheden eller nemheden eller dispergerbarheden af PMCM-forbindelsen i dis-pergeringsraidlet er, desto mindre middel vil der kræves, og 30 den efterfølgende fjernelse af midlet vil blive lettet.The agent must be capable of dissolving or dispersing a desired PMCM compound at the temperature used to form the original mixture, without adversely affecting the phytoactivity of the PMCM compound. The greater the solubility or ease or dispersibility of the PMCM compound in the dispersing eye, the less agent will be required and the subsequent removal of the agent will be facilitated.
Foretrukne dlspergeringsxnidler omfatter vand og polære, organi ske opløsningsmidler, såsom methanol, ethanol, isopropylalkohol og acetone. Vand er det mest foretrukne.Preferred dispersing agents include water and polar organic solvents such as methanol, ethanol, isopropyl alcohol and acetone. Water is the most preferred.
16 DK 173955 B116 DK 173955 B1
De herbicide midler, der tilvejebringes i overensstemmelse med 5 denne opfindelse, er effektive, når de fortyndes med vand og påføres til det ønskede sted ved sprøjtning eller på anden måde. Påføringsstedet kan være jord, frø, kimplanter eller de faktiske planter samt indhegnede (eng.: fettered) marker. Der foretrækkes påføring på bladene. Midlerne kan påføres ved anvendel-10 se af bom- og håqdsprøjteapparater og kan også påføres ved sprøjtning fra flyvemaskiner, fordi de er effektive i meget lave doser.The herbicidal agents provided in accordance with this invention are effective when diluted with water and applied to the desired site by spraying or otherwise. The site of application may be soil, seeds, seedlings or the actual plants as well as fenced red fields. Preference is given to the leaves. The agents can be applied by the use of boom and head sprayers and can also be applied by spraying from airplanes because they are effective at very low doses.
Herbicid-undersøgelser:Herbicide studies:
Som tidligere nævnt, er de heri beskrevne PMCM-forbindelser fytotoksiske forbindelser, som er nyttige og værdifulde til regule-15 ring af forskellige plantearter. Udvalgte forbindelser ifølge denne opfindelse blev testet som herbicider på følgende måde;As previously mentioned, the PMCM compounds described herein are phytotoxic compounds that are useful and valuable for regulating various plant species. Selected compounds of this invention were tested as herbicides in the following manner;
Post-emergens-herbicidtest: På den tiende dag før behandling blev frø af forskellige ukrudtsarter plantet i leret sandjord i individuelle rækker under an-20 vendelse af én art pr. række i en plantekasses bredde. De anvendte frø var Johnsongræs (Echinochloa crusgalli), étårig konge for en dag (Ipomoea lacunosa) , fløjlsbladr (Abutilon theo-phrasti), Bermudagræs (Cynodon dactylon), gul nøddestar (Cyperus esculentus) og violet nøddestar (Cyperus rotundus). Oer blev plantet 25 rigelige mængder frø for at give ca. 20 - 40 kimplanter pr. række efter emergens, afhængigt af planternes størrelse.Post-emergence herbicide test: On the tenth day before treatment, seeds of different weed species were planted in clay sandy soil in individual rows using one species per day. row in the width of a plant box. Seeds used were Johnson grass (Echinochloa crusgalli), one-year-old king for a day (Ipomoea lacunosa), velvet leaf (Abutilon theo-phrasti), Bermuda grass (Cynodon dactylon), yellow nut star (Cyperus esculentus) and violet nut desert. Oer was planted 25 copious amounts of seeds to yield approx. 20 - 40 seedlings per row by emergence, depending on the size of the plants.
Der fremstilledes en serie formuleringer ved at kombinere tri- DK 173955 B1 17 methylsulfoniumsaltet af N-phosphomethylglycin (TMP) med forskellige overfladeaktive midler og vand. I formulering nr. 1 i den efterfølgende tabel refererer betegnelsen "TMP 4-LC(B)" til en formulering, omfattende 73,7 vægt% af en vandig opløsning 5 af trimethylsulfoniumsaltet af N-phosphonomethylglycin (55,9% aktiv bestanddel), 20,6 vægt% af et overfladeaktivt middel og 5,7 vægt% vand. I hver af de nedenfor angivne andre formuleringer er der foretaget numerisk korrelation mellem formuleringen og formuleringerne i tabellen. I de angivne formuleringer er 10 den aktive bestanddel (TMP) angivet, og ved siden deraf er angivet procentsatsen af aktiv bestanddel i opløsningen. Det overfladeaktive middel er ligeledes angivet som havende en specifik procent renhed, hvilket er angivet ved siden af det aktive middels kemiske navn.A series of formulations were prepared by combining the tri-methylsulfonium salt of N-phosphomethylglycine (TMP) with various surfactants and water. In formulation # 1 in the following table, the term "TMP 4-LC (B)" refers to a formulation comprising 73.7% by weight of an aqueous solution 5 of the trimethylsulfonium salt of N-phosphonomethylglycine (55.9% active ingredient), 20.6% by weight of a surfactant and 5.7% by weight water. In each of the other formulations listed below, numerical correlation has been made between the formulation and the formulations in the table. In the formulations indicated, the active ingredient (TMP) is indicated and the percentage of active ingredient in the solution is indicated next to it. The surfactant is also indicated as having a specific percent purity, which is indicated next to the chemical name of the active agent.
15 i testproceduren blev hver individuel formulering opløst i vand, og der anvendtes forskellige portioner vand til at fortynde formuleringens koncentration for at opnå den ønskede påføringsmængde.In the test procedure, each individual formulation was dissolved in water and different portions of water were used to dilute the concentration of the formulation to obtain the desired amount of application.
Efter at den ønskede fortynding var opnået, blev opløsningen derefter sprøjtet på en tilsået plantekasse på et lineært sprøjte-20 bånd,, som var kalibreret til at give 748 liter pr. hektar.After the desired dilution was achieved, the solution was then sprayed onto a sown plant box on a linear syringe band, calibrated to yield 748 liters per liter. acres.
Efter behandling placeredes plantekasserne i et drivhus ved en temperatur på 21 - 27°C og vandedes ved overbrusning. 2 uger efter behandling bestemtes graden af skade eller regulering ved sammenligning med ubehandlede kontrolplanter på samme alder.After treatment, the plant boxes were placed in a greenhouse at a temperature of 21 - 27 ° C and irrigated by showering. Two weeks after treatment, the degree of damage or regulation was determined by comparison with untreated control plants of the same age.
25 Skadevurderingen fra 0 til 100% registreredes for hver art som procent regulering, idet 0% angiver ingen skade, og 100% angiver fuldstændig regulering.25 The damage rating from 0 to 100% for each species was recorded as percent regulation, with 0% indicating no damage and 100% indicating complete regulation.
Resultaterne af forsøgene er vist i de følgende tabeller.The results of the experiments are shown in the following tables.
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_ . Etårig_. annual
Formel Mængde , Gul konge forFormal Quantity, Yellow King for
Formulering (a.b.) iag/mr Fløjlsblad nøddestar en dag 1. IMP 57,3% 71,9 (41,2) 56 40 40 40 272 20'6 112 70 70 100Formulation (please) iag / mr Velvet leaf nutstars one day 1. IMP 57.3% 71.9 (41.2) 56 40 40 40 272 20'6 112 70 70 100
Vand 7,5 224 95 90 100 100,0% 5 2. TMP 57,3% 71,9 (41,2) 56 30 30 30 ^J^7513 20,6 112 60 60 70Water 7.5 224 95 90 100 100.0% 5 2. TMP 57.3% 71.9 (41.2) 56 30 30 30 ^ J ^ 7513 20.6 112 60 60 70
Vand 7,5 224 95 90 95 100,0% 3. TMP 57,3% 71,9 (41,2) 56 40 40 40 1° anool^D-7533 20,6 112 70 70 iooWater 7.5 224 95 90 95 100.0% 3. TMP 57.3% 71.9 (41.2) 56 40 40 40 1 ° anole ^ D-7533 20.6 112 70 70 ioo
Vand 7,5 224 98 95 100 100,0% 4. TMP 57,5% . 71,7 (41,2) 56 40 50 30 APG 23-3 100% 20,6 (9,5) 112 60 90 50 15 Vand 7,7 224 90 100 80 100,0% 5. TMP 57,5% 71,7 (41,2) 56 30 40 30 APG 91-1 51% 20,6 (10,5) 112 60 70 50Water 7.5 224 98 95 100 100.0% 4. TMP 57.5%. 71.7 (41.2) 56 40 50 30 APG 23-3 100% 20.6 (9.5) 112 60 90 50 15 Water 7.7 224 90 100 80 100.0% 5. TMP 57.5% 71.7 (41.2) 56 30 40 30 APG 91-1 51% 20.6 (10.5) 112 60 70 50
Vand 7,7 224 90 100 80 100,0% 6. TMP 57,5% 71,7 (41,2) 56 40 50 30 20 APG 91-3 57% 20,6 (11,7) 112 80 90 50Water 7.7 224 90 100 80 100.0% 6. TMP 57.5% 71.7 (41.2) 56 40 50 30 20 APG 91-3 57% 20.6 (11.7) 112 80 90 50
Vand 7,7 224 100 100 80 100'0% (forts.) 25 DK 173955 B1Water 7.7 224 100 100 80 100'0% (cont.) 25 DK 173955 B1
Etårig Mængde, Gul konge forOne Year Quantity, Yellow King for
Formulering mg/ir/ Fløjlsblad nøddestar en dagFormulation mg / ir / Velvet leaf nutstars one day
Kontrol 0 0 0 0Control 0 0 0 0
Kontrol 0 0 0 0 a.b. = aktiv bestanddel.Control 0 0 0 0 a.b. = active ingredient.
Den mængde af det foreliggende middel, som udgør en herbicidt effektiv mængde, afhænger af naturen af de frø eller planter, der 2 5 skal reguleres. Påføringsmængden varierer fra ca. 1,1 mg/m til 2 2 ca. 5,6 g/m (a.b.), fortrinsvis fra ca. 11 mg/m til ca. 2,8 g/ m (a.b.), idet den faktiske mængde afhænger af den totale omkostning og de ønskede resultater. Det vil nemt fremgå for fagfolk inden for området, at midler, der udviser en lokal herbicid 10 aktivitet, vil kræve en højere dosis end.mere aktive forbindelser til den samme reguleringsgrad.The amount of the present agent which constitutes a herbicidally effective amount depends upon the nature of the seeds or plants to be regulated. The amount of application varies from approx. 1.1 mg / m to 2 2 approx. 5.6 g / m (a.b.), preferably from ca. 11 mg / m to approx. 2.8 g / m (a.b.), the actual amount being dependent on the total cost and results desired. It will be readily apparent to those skilled in the art that agents exhibiting a local herbicide activity will require a higher dose than more active compounds of the same degree of regulation.
Anvendt heri henviser udtrykket "herbicid" til en forbindelse, som regulerer eller modificerer plantevækst, f.eks. aflivning, forsinkelse, afløvning, udtørring, regulering, forkrøbling, sætning 15 af skud fra stængelen og dværgvækst. "Plante" henviser til alle fysiske dele, herunder frø, kimplanter, unge træer, rødder, knolde, stilke, stængler, blade og frugter. "Plantevækst" skal omfatte alle udviklingsfaser fra frøspiring til naturlig eller induceret standsning af liv.As used herein, the term "herbicide" refers to a compound that regulates or modifies plant growth, e.g. killing, delaying, draining, desiccating, regulating, crippling, sentence 15 of shoot from the stem and dwarf growth. "Plant" refers to all physical parts, including seeds, seedlings, young trees, roots, tubers, stems, stems, leaves and fruits. "Plant growth" shall include all stages of development from seed germination to natural or induced cessation of life.
Claims (7)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US78985485A | 1985-10-21 | 1985-10-21 | |
US78985485 | 1985-10-21 |
Publications (3)
Publication Number | Publication Date |
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DK504886D0 DK504886D0 (en) | 1986-10-21 |
DK504886A DK504886A (en) | 1987-04-22 |
DK173955B1 true DK173955B1 (en) | 2002-03-11 |
Family
ID=25148858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK198605048A DK173955B1 (en) | 1985-10-21 | 1986-10-21 | Liquid herbicide concentrate and its use in a method for controlling undesirable vegetation |
Country Status (15)
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EP (1) | EP0220902B1 (en) |
JP (1) | JPH0784367B2 (en) |
AT (1) | ATE164726T1 (en) |
AU (1) | AU591938B2 (en) |
BR (1) | BR8605102A (en) |
DE (1) | DE3650670T2 (en) |
DK (1) | DK173955B1 (en) |
ES (1) | ES2113844T3 (en) |
FI (1) | FI88666C (en) |
GR (1) | GR3026574T3 (en) |
HU (1) | HU208239B (en) |
IL (1) | IL80372A (en) |
NO (1) | NO170452C (en) |
NZ (1) | NZ217999A (en) |
ZA (1) | ZA867926B (en) |
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ES2033569B1 (en) * | 1990-12-31 | 1993-12-16 | En E Ind Aragonesas | HERBICIDE CONCENTRATED COMPOSITIONS, PROCEDURE FOR THEIR OBTAINING AND EMPLOYMENT. |
DK0498145T3 (en) * | 1991-02-08 | 1996-01-02 | Monsanto Europe Sa | Solid glyphosate compositions and their use |
CA2075003C (en) * | 1991-08-02 | 1999-01-19 | James Web Kassebaum | Herbicidal compositions and methods of preparing and using the same |
US5258359A (en) * | 1991-08-02 | 1993-11-02 | Monsanto Company | Glyphosant-containing herbicidal compositions comprising acetylenic diol rainfastness enhancing agents |
JPH0543403A (en) * | 1991-08-08 | 1993-02-23 | Kao Corp | Agent for promoting activity of biocide and agricultural chemical composition |
US5385750A (en) * | 1992-05-14 | 1995-01-31 | Henkel Corporation | Alkyl glycoside compositions with improved wetting properties |
SE506265C2 (en) * | 1995-04-28 | 1997-11-24 | Akzo Nobel Nv | Aqueous composition containing an alkyl glycoside and its use as a wetting agent |
AUPO405696A0 (en) | 1996-12-06 | 1997-01-09 | Ici Australia Operations Proprietary Limited | Herbicidal compositions |
TW529910B (en) | 1997-01-30 | 2003-05-01 | Basf Ag | Solid mixtures based on sulfonylureas and adjuvants |
EP0931580B1 (en) * | 1997-05-21 | 2003-08-13 | Maeda Limited | Filter for compressed air |
US6127317A (en) * | 1997-09-17 | 2000-10-03 | American Cyanamid Company | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
GB9720891D0 (en) * | 1997-10-02 | 1997-12-03 | Ici Plc | Agrochemical compositions |
US6214768B1 (en) | 1998-09-14 | 2001-04-10 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
US6277787B1 (en) | 1998-09-14 | 2001-08-21 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
FR2811514B1 (en) * | 2000-07-11 | 2003-01-24 | Seppic Sa | HERBICIDE COMPOSITION COMPRISING GLYPHOSATE AND AT LEAST ONE ALKYL POLYXYLOSIDE |
DE10052489A1 (en) | 2000-10-23 | 2002-05-02 | Hermania Dr Schirm Gmbh | Solid glyphosate formulation and method of manufacture |
EP2337452B1 (en) | 2008-07-03 | 2014-11-05 | Monsanto Technology LLC | Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants |
EP2329715B1 (en) * | 2009-12-01 | 2013-02-20 | Cognis IP Management GmbH | Biocide compositions comprising branched alkyl polyglycosides |
US8551533B2 (en) | 2011-05-09 | 2013-10-08 | Momentive Performance Materials Inc. | Adjuvant composition and agrochemical formulation containing same |
WO2013129496A1 (en) | 2012-02-27 | 2013-09-06 | ナブテスコオートモーティブ 株式会社 | Oil separator |
US10082057B2 (en) | 2012-02-27 | 2018-09-25 | Nabtesco Automotive Corporation | Oil separator |
EP2821605B1 (en) | 2012-02-27 | 2022-01-12 | Nabtesco Automotive Corporation | Oil separator |
IN2014MN02671A (en) | 2012-07-02 | 2015-08-28 | Nabtesco Automotive Corp |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
EG13404A (en) * | 1977-05-16 | 1981-06-30 | Monsanto Co | Corrosion inhibited agriculturai compositions |
IE50142B1 (en) * | 1979-07-11 | 1986-02-19 | Sampson Michael James | Improved method of using a plant-growth regulator |
US4315765A (en) * | 1980-12-04 | 1982-02-16 | Stauffer Chemical Company | Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides |
US4384880A (en) * | 1980-12-04 | 1983-05-24 | Stauffer Chemical Company | Trialkylsulfonium salts of N-phosphonomethyl-glycine and their use as plant growth regulators and herbicides |
AU556954B2 (en) * | 1981-08-24 | 1986-11-27 | Stauffer Chemical Company | Phosphonium salts of n-phosphono-methylglycine and their use as herbicides and plant growth regulators |
GB2129303B (en) * | 1982-11-03 | 1986-10-29 | Silver Clouds Sdn Bhd | Herbicide |
-
1986
- 1986-10-17 BR BR8605102A patent/BR8605102A/en unknown
- 1986-10-20 AU AU64191/86A patent/AU591938B2/en not_active Withdrawn - After Issue
- 1986-10-20 NZ NZ217999A patent/NZ217999A/en unknown
- 1986-10-20 HU HU864348A patent/HU208239B/en unknown
- 1986-10-20 FI FI864231A patent/FI88666C/en not_active IP Right Cessation
- 1986-10-20 DE DE3650670T patent/DE3650670T2/en not_active Expired - Lifetime
- 1986-10-20 ZA ZA867926A patent/ZA867926B/en unknown
- 1986-10-20 EP EP86308108A patent/EP0220902B1/en not_active Expired - Lifetime
- 1986-10-20 NO NO864182A patent/NO170452C/en unknown
- 1986-10-20 AT AT86308108T patent/ATE164726T1/en not_active IP Right Cessation
- 1986-10-20 IL IL80372A patent/IL80372A/en not_active IP Right Cessation
- 1986-10-20 ES ES86308108T patent/ES2113844T3/en not_active Expired - Lifetime
- 1986-10-21 DK DK198605048A patent/DK173955B1/en not_active IP Right Cessation
- 1986-10-21 JP JP61250600A patent/JPH0784367B2/en not_active Expired - Lifetime
-
1998
- 1998-04-09 GR GR980400486T patent/GR3026574T3/en unknown
Also Published As
Publication number | Publication date |
---|---|
NZ217999A (en) | 1989-10-27 |
AU591938B2 (en) | 1989-12-21 |
BR8605102A (en) | 1987-07-21 |
ES2113844T3 (en) | 1998-05-16 |
FI864231A0 (en) | 1986-10-20 |
NO864182D0 (en) | 1986-10-20 |
NO170452C (en) | 1992-10-21 |
FI88666C (en) | 1993-06-28 |
FI864231A (en) | 1987-04-22 |
NO864182L (en) | 1987-04-22 |
IL80372A0 (en) | 1987-01-30 |
GR3026574T3 (en) | 1998-07-31 |
ZA867926B (en) | 1987-11-25 |
DE3650670T2 (en) | 1998-07-30 |
DE3650670D1 (en) | 1998-05-14 |
FI88666B (en) | 1993-03-15 |
JPS6299313A (en) | 1987-05-08 |
IL80372A (en) | 1991-12-12 |
DK504886D0 (en) | 1986-10-21 |
EP0220902B1 (en) | 1998-04-08 |
JPH0784367B2 (en) | 1995-09-13 |
EP0220902A3 (en) | 1989-08-23 |
ATE164726T1 (en) | 1998-04-15 |
AU6419186A (en) | 1987-04-30 |
HU208239B (en) | 1993-09-28 |
EP0220902A2 (en) | 1987-05-06 |
HUT44141A (en) | 1988-02-29 |
NO170452B (en) | 1992-07-13 |
DK504886A (en) | 1987-04-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
B1 | Patent granted (law 1993) | ||
PUP | Patent expired |